Acetone → HCID 117774395, compound

HRID 2281088Notes

Reaction equation

HRID 2281088 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C@H:7]([O:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:8])[O:4][N:3]=1.CC(C)=O.[NH4+].[Cl-]>O.CCOC(C)=O.[Cl-].[Ti+3].[Cl-].[Cl-]>[CH3:1][C:2]1[CH:6]=[C:5]([C@H:7]([O:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:8])[O:4][N:3]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 117774754HCID 117774754, compound

Product 1

HCID 117774395HCID 117774395, compound

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 0.5 g (2.09 mmol) 3-methyl-5-[(1R)-1-[(3-nitro-2-pyridyl)oxy]ethyl]isoxazole and acetone are cooled to 5° C. and 87 ml (17.4 mmol) of titanium(III)chloride 20% in water and 24 ml (96 mmol) of a 4M solution of NH4Cl in water are added. The mixture is warmed to RT and stirred over night diluted with EtOAc and water. The organic layer is separated and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried and evaporated. The residue is purified by FC (DCM/MeOH 95:5).

Workup

  1. temperatureThe mixture is warmed to RT
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. customdried
  6. customevaporated
  7. customThe residue is purified by FC (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-aa5890b415ba4022a9763879bad68ed6
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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